Her stage role in A Midsummer Night’s Dream led to the movie of the same name, and by the same director, and that led her to a contract with Warner Bros. Her later conflict with the studio resulted in a court case that gave all actors more freedom.
Her most frequent co-star was Errol Flynn. They worked together in eight films: The Adventures of Robin Hood (1938), Captain Blood (1935), The Charge of the Light Brigade (1936), Dodge City (1939), Four’s a Crowd (1938), The Private Lives of Elizabeth and Essex (1939), Santa Fe Trail (1940), and They Died with Their Boots On (1941), and appeared separately in a ninth film, Thank Your Lucky Stars (1943).
She was frequently directed by Michael Curtiz, who she hated as a tyrant, though she admitted that he was a great director who know how to tell stories.
Two of her most acclaimed films don’t make my list. The Heiress gets by on one memorable speech, but the rest is slow and unengaging; it contains one of the worst performances in the golden age of film as Montgomery Clift searches for an accent. As for The Snake Pit, the music is bombastic and it is edited like a ‘50s exploitation thriller. It is one of those films that got credit for its social effect; it was responsible for improvements in the US mental health system. It was more important than great.
First, a dishonorable mention for her weak silly performance as Melanie in the atrocious Gone with the Wind (full review here).
And an honorable mention for The Dark Mirror, where de Havilland gives one of her best performances as a pair of twins, one evil. It gets a bit silly and becomes far too predictable, but it has a nice Noir style.
#8 – Light in the Piazza (1962) — A surprising good film they’d never make today. Olivia de Havilland plays the mother of a girl whose brain injury keeps her as a mental ten-year-old. Now beautiful and in her twenties, she catches the eye of a rich and suave Italian who is attracted to her love of life. de havilland wins on acting, but Yvette Mimieux and George Hamilton steal the picture based on pure charisma. This is a thoughtful and romantic film.
#7 – The Charge of the Light Brigade (1936) — The least of the major British-in-colonial-India adventure films, mainly due to the weak romance (poor Olivia de Havilland gets stuck with the worst role of her career). It is also bizarrely historically inaccurate (they didn’t even get the guns right, much less the reason for the charge) and the production was so vile it caused animal welfare laws to be passed. But Errol Flynn is charming, the combat exciting, and it all looks spectacular. [Also on the Errol Flynn list]
#6 – Four’s a Crowd (1938) — Errol Flynn is a charming cad who runs positive PR for the worst people and de Havilland is the spoiled and silly daughter of one of those terrible people. It’s a romantic comedy that also includes Rosalind Russell and Flynn & de Havilland’s frequent co-star, Patric Knowles. [Also on the Errol Flynn list]
#5 – My Cousin Rachel (1952) — A gothic love story and mystery. Is de Havilland a murderess or is Philip just a fool? Well, Philip is certainly a fool in any case. Richard Burton seems too old for the part of a naive youth (Burton never appeared young), but is still compelling. de Havilland is stunning, and I can believe Philip falling instantly for her.
#4 – It’s Love I’m After (1937) — An unfairly forgotten farce, with Leslie Howard as a ham actor in a tempestuous relationship with Bette Davis’s equally over-the-top actress. (It was their third collaboration). Olivia de Havilland, looking like a teenager, plays a girl obsessed by Howard’s Basil Underwood. Both Howard and Davis are naturals at playing hams.
#3 – The Great Garrick (1937) — One of the best comedies of ’37, in which a band of French actors attempt to humiliate the English star David Garrick by pretending to be all of the workers and guests at a country inn, but things become complicated when an unconnected woman (Olivia de Havilland) stumbles into their performance. The supporting cast, including Edward Everett Horton, are as good as the leads.
#2 – Captain Blood (1935) — The first of the de Havilland/Flynn films and the first true Swashbuckler of the Sound era. Errol Flynn is a physician forced into piracy and she’s the governor’s daughter. (Full Critique) [Also on the Errol Flynn list and Basil Rathbone list]
#1 – The Adventures of Robin Hood (1938) — The greatest classic Swashbuckler and one of the Best films ever made. It is beautifully shot, with a wonderful score and a strong supporting cast, including de Havilland. It is here that Errol Flynn became an icon. (Full Critique) [Also on the Errol Flynn list and Basil Rathbone list]